Hollywood has depicted some interesting races over the years. Gumball Rally, Cannonball Run, Rat Race, and Speed Zone were about as close as most of us could probably get to living out our automotive fantasies on public roads. But what if someone actually took an idea like that and made an event out of it? Although it’s really fodder for its own cinematic homage, the Gambler 500 is exactly that. We’re not talking the usual “who can make it to the finish line first” type deal. It’s all about fun on four wheels, friendship, and Oregon sightseeing with a lynchpin that involves some rather whimsical and resourceful innovation with cars that probably didn’t have much of a future. Google some of the images of this event and you might think it’s a mad mad mad mad world. Participate in it, and you’ll walk away counting down the days until the next one.

It defies conventional categorization. We hesitate to use the word “race” in describing it, as the preferred nomenclature is “rally.” The event’s taglines are “fun is greater than rules” and “don’t be a dick.” We think those are pretty self-explanatory. No, the Gambler 500 isn’t a cosplay event like the MadMax-themed Wasteland Weekend, nor is it a balls-to-the wall adrenaline dump like the Baja 1000, nor some hackneyed demolition derby where cars and property are intentionally destroyed and abandoned. This is an exercise in automotive adventure.

The Gambler 500 began in 2014 as an exercise in bragging rights but is now a source of national attention, with participants venturing from the far reaches of the country for a spot in this one-of-a-kind event. The idea came about when the Gambler’s impresario, Tate Morgan, began discussing how to create an unusual challenge among friends. It was never originally intended to be a commercial venture or open to the general public. The unique appeal of the Gambler 500 eventually spread like word of a high school kegger after Chubbies clothing shared some clips of their first few events online. It looked like the most (and cheapest) fun anyone could have with a car. The tidal wave of interest was too much to keep it a secret anymore.

Here’s the premise: Buy a car for no more than $500. Put as much money as you want into it afterward, but drive it from point A to point B with waypoints in between, enjoying the Oregon landscape and helping others who may be sidelined with repairs. Sure, you could show up in a new 4×4 telling people you only spent $500, but what kind of challenge or fun would that be? The point is to see if you can assemble a crew of navigators, other drivers, and impromptu mechanics to make the trek in something whose performance is questionable at best. It’s an A to B rally, but the A is wherever you start from as long as you record how much off-roading you did, which should equate to roughly 500 miles when it’s all said and done.

Last year, RECOIL teamed up with staff from Salient Arms, Noveske, and SIG SAUER, who brought everything from two Crown Vics, a ’70s Javelin, a ’90s Mustang, and a “boat car.” Previous RECOIL vehicles include a vintage fire truck and an ’80s Toyota van. As you can see by some of the other cars pictured, entrants are encouraged to think outside the box with their choice of transportation. The wilder and more impractical, the better.

How do you determine the amount of off-road covered, you ask? “Last year, we developed an app. We use a technology solution, which I think actually made the rally better. It measures your percentage of off-road taken,” Morgan says. “So, if I’m in Portland and going to head down to Chemult where our camp was this year, since the competition isn’t about speed or time, but the percentage of off-road taken, I can’t take I-5 down and cut over on another highway. That way I’ve gotta kinda get out a map and discover my own way, because if there’s 1,700 other cars doing the same thing, but are starting at different times, going different ways, and from different places, we’re not concentrating everyone on one particular road.”

“Boats ‘n Hoes” was the salient theme — though they got tired of hearing it sung by the end of the Gambler.

To accommodate the ever-increasing number of entrants participating, keep things interesting, and introduce you to some hidden gems of the Oregon countryside, the event also changes format each year. You might think that an event with this many people traversing rural back roads and public land would lead to something that resembled the aftermath of an Occupy gathering. Quite the opposite.

Morgan had the foresight to incorporate a trail cleanup into the Gambler as well. “We’re currently the largest trail cleanup in the world because we challenge every one of our 4,000 participants to bring back as much garbage as they can,” he says. Big names such as Yakima, Benchmade, and SIG SAUER (the 2018 event’s presenting sponsor) incentivize the effort by offering prizes for whoever collects the most trash.

You may also assume that people ditch their cars after the race, forcing the locals to figure out what to do with them, but in the past Morgan has arranged for cars entrants didn’t want to hang onto to be auctioned off for charity. Nowadays it seems as if people are more inclined to keep their cars for future races … or just maybe for the hell of it. How many events can you think of that have that sort of environmental concern, philanthropy, and conservation as part of their focus? Didn’t think so.

Considering trying out your automotive ingenuity at the Gambler? Morgan suggests keeping it challenging by buying something simple and two-wheel drive that’s not the most obvious choice. As long as you have a keen sense of outdoor adventure, that’s really the only prerequisite for participation. Big egos need not apply. The guy with the cheapest, dumbest car who was slowest to arrive at the campsite rally points will be the one who really embodies the spirit of the event. That’s what makes it fun.

The Gambler 500 is a competition focused on how much you can do with how little. It keeps people coming back year after year and shows no signs of slowing down. In fact, plans to expand the event to other locations are also in the works. Want to see more of what it’s all about? Check out some of RECOIL’s participation in the Gambler 500 at www.recoil.tv.